JPH10139772A - Optically active lactones - Google Patents
Optically active lactonesInfo
- Publication number
- JPH10139772A JPH10139772A JP8311408A JP31140896A JPH10139772A JP H10139772 A JPH10139772 A JP H10139772A JP 8311408 A JP8311408 A JP 8311408A JP 31140896 A JP31140896 A JP 31140896A JP H10139772 A JPH10139772 A JP H10139772A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- liquid crystal
- ring
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002596 lactones Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000004973 liquid crystal related substance Substances 0.000 claims description 16
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 6
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 abstract description 17
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 abstract description 3
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 abstract description 3
- 125000000686 lactone group Chemical group 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 238000007796 conventional method Methods 0.000 abstract 1
- 230000004043 responsiveness Effects 0.000 abstract 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- -1 lactone compound Chemical class 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 230000004044 response Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- KZIZPXDIBXXKAJ-UHFFFAOYSA-N 1-heptyl-4-phenylbenzene Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=CC=C1 KZIZPXDIBXXKAJ-UHFFFAOYSA-N 0.000 description 2
- CYRPYGNRBTZSPG-UHFFFAOYSA-N 5-butyl-3-propyloxolan-2-one Chemical compound CCCCC1CC(CCC)C(=O)O1 CYRPYGNRBTZSPG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
- 229940063656 aluminum chloride Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- NMOFYYYCFRVWBK-SSDOTTSWSA-N (2r)-2-pentyloxirane Chemical compound CCCCC[C@@H]1CO1 NMOFYYYCFRVWBK-SSDOTTSWSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229940055858 aluminum chloride anhydrous Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、液晶表示素子、特
に強誘電性液晶表示素子に好適に使用できる、光学活性
な化合物、およびそれを用いた液晶組成物、強誘電性液
晶表示素子に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an optically active compound, a liquid crystal composition using the same, and a ferroelectric liquid crystal display device which can be suitably used for a liquid crystal display device, particularly a ferroelectric liquid crystal display device.
【０００２】[0002]
【従来の技術】現在、液晶表示素子は広汎に使用される
に至っている。それらのうち、低品位の表示素子として
は、ＴＮ（捻れネマチック）型表示方式が最も広く使用
されている。このＴＮ表示は低駆動電圧、低消費電力な
どの利点を多く備えている。しかしながら応答速度に関
しては、陰極管、エレクトロルミネッセンス、プラズマ
ディスプレイ等の発光型の表示素子に著しく劣ってい
る。捻れ角を１８０゜〜２７０゜にした新しいタイプの
ＴＮ表示素子、いわゆるＳＴＮ表示素子が開発されて、
表示容量は飛躍的に増大したが、応答速度に関してはや
はり限界がある。また、最近ではＴＮ表示素子の各画素
にスイッチ素子を備え付けた表示素子が、市場に登場し
ている。その多くは、薄膜トランジスター素子（Ｔｈｉ
ｎ Ｆｉｌｍ Ｔｒａｎｓｉｓｔｏｒ）、略称してＴＦ
Ｔ型と呼ばれており、高密度、大容量かつフルカラーの
液晶素子として、将来を嘱望されてる。しかし、この方
式も画面サイズと生産コストに難点があげられている。
ＴＦＴは半導体技術を用いているため、画面サイズが二
十数インチサイズが限界であり、また同様に、時分割能
も１０００ライン程度が限界である、といわれている。
本発明の主題である強誘電性液晶表示素子は、上記ＴＦ
Ｔ素子が実現できない、二十数インチサイズ以上の大画
面と生産コストの低減の両者の実現の可能性を秘めてい
る。（クラークら；アプライド フィジクス レター
（ＡｐｐｌｉｅｄＰｈｙｓ．ｌｅｔｔ．，）３６，８９
９（１９８０））。この表示方式は、強誘電性を示すカ
イラルスメクチックＣ相（以下Ｓｃ＊相と略記する）等
のカイラルスメクチック相を利用する。 上記の方法は、
表面安定化強誘電性液晶表示と呼ばれ、家電メーカーや
材料メーカーによって製品化に取り組まれており、特性
の改良や商品化が行われている。その理由は、強誘電性
液晶素子が原理的に下記１〜３の特徴を有するからであ
る。 １．高速応答性 ２．メモリー性 ３．広視野角 これらの特徴がＳＳＦＬＣの大容量表示への可能性を示
唆しており、ＳＳＦＬＣを非常に魅力あるものにしてい
る。一般に、液晶組成物は液晶化合物あるいは非液晶化
合物からでも構成できる。強誘電性液晶組成物は強誘電
性液晶化合物のみから構成する方法、非カイラルなスメ
クチックＣ，Ｆ，Ｇ，Ｈ，Ｉ等の傾いたスメクチック相
（以下、Ｓｃ等の相と略記する）を呈する化合物及び組
成物を基本物質として、１種以上の強誘電性液晶化合物
あるいは非液晶の光学活性化合物を混合することによ
り、全体を強誘電性液晶相を呈する組成物となし得る方
法がある。2. Description of the Related Art At present, liquid crystal display devices have been widely used. Among them, a TN (twisted nematic) display method is most widely used as a low-quality display element. This TN display has many advantages such as low driving voltage and low power consumption. However, the response speed is remarkably inferior to light-emitting display elements such as a cathode ray tube, electroluminescence, and a plasma display. A new type of TN display element having a twist angle of 180 ° to 270 °, a so-called STN display element, has been developed.
Although the display capacity has increased dramatically, there is still a limit to the response speed. Recently, a display element in which a switch element is provided in each pixel of the TN display element has appeared on the market. Many of them are thin film transistor elements (Thi
n Film Transistor), abbreviated as TF
It is called a T-type, and is expected to have a future as a high-density, large-capacity, full-color liquid crystal element. However, this method also has drawbacks in screen size and production cost.
It is said that the TFT has a screen size of about twenty and a few inches because of the use of semiconductor technology, and also has a time division capability of about 1000 lines.
The ferroelectric liquid crystal display element which is the subject of the present invention is characterized in that
It has the potential of realizing both a large screen of more than twenty inches size, which cannot realize a T element, and a reduction in production cost. (Clark et al., Applied Physics Letter, 36, 89).
9 (1980)). This display method uses a chiral smectic phase such as a chiral smectic C phase (hereinafter abbreviated as Sc * phase) exhibiting ferroelectricity. The above method
It is called a surface-stabilized ferroelectric liquid crystal display, and is being commercialized by home appliance manufacturers and material manufacturers, and its characteristics are being improved and commercialized. The reason is that the ferroelectric liquid crystal element has the following features 1 to 3 in principle. 1. High-speed response 2. 2. Memory properties Wide viewing angle These features suggest the potential of SSFLC for large capacity displays, making SSFLC very attractive. Generally, the liquid crystal composition can be composed of a liquid crystal compound or a non-liquid crystal compound. The ferroelectric liquid crystal composition is composed of only a ferroelectric liquid crystal compound, and exhibits a non-chiral smectic C, F, G, H, I or other inclined smectic phase (hereinafter abbreviated as a phase such as Sc). There is a method in which a compound exhibiting a ferroelectric liquid crystal phase can be formed as a whole by mixing one or more ferroelectric liquid crystal compounds or a non-liquid crystal optically active compound with a compound or a composition as a basic substance.
【０００３】これまでにラクトン環を含有する強誘電性
液晶用の光学活性化合物はいくつか発表されてきた。こ
れらの化合物は、強誘電性液晶組成物用の光学活性添加
剤として非常に有用であることが示されている。Several optically active compounds for ferroelectric liquid crystals containing a lactone ring have been disclosed so far. These compounds have been shown to be very useful as optically active additives for ferroelectric liquid crystal compositions.
【０００４】[0004]
【化４】 Embedded image
【化５】 Embedded image
【０００５】さらに、本発明者らは、先に以下の化合物
を報告した。The present inventors have previously reported the following compounds.
【０００６】[0006]
【化６】 Embedded image
【０００７】（ここでｎ＝０−２である。）(Here, n = 0-2)
【０００８】[0008]
【発明が解決しようとする課題】しかし、上記の光学活
性ラクトン系化合物においてフェニル基とラクトン環に
挟まれたメチレン鎖長と液晶物性との間の相関関係は十
分に解明された訳ではない。そこで、本発明者らは、特
に上記の化合物を更に拡張して、上記のｎを大きくし
て、その特性を調査することを目的とし、強誘電性液晶
組成物に添加するに十分の特性を有する光学活性化合物
の開発を目的とした。However, the correlation between the phenyl group and the length of the methylene chain sandwiched between the lactone rings and the physical properties of the liquid crystal in the above-mentioned optically active lactone compound has not been fully elucidated. Then, the present inventors have further expanded the above-mentioned compound, aimed at increasing the above-mentioned n and investigating its properties, and have found that the properties sufficient for addition to the ferroelectric liquid crystal composition are obtained. The aim was to develop an optically active compound having the same.
【０００９】[0009]
【課題をを解決するための手段】すなわち、本発明は下
記（１）〜（３）の構成を有する。 （１）一般式（１）で表される化合物That is, the present invention has the following constitutions (1) to (3). (1) Compound represented by general formula (1)
【化７】 （ただし（１）式において、Ｒは炭素数１−１６のアル
キル基、アルコキシ基、Ｒ’は炭素数１−１２のアルキ
ル基を示す、環Ａは１，４−フェニレン基または１，４
−シクロヘキシレン基、または単結合を示す。）Embedded image (However, in the formula (1), R represents an alkyl group having 1 to 16 carbon atoms, an alkoxy group, R ′ represents an alkyl group having 1 to 12 carbon atoms, and ring A represents 1,4-phenylene group or 1,4
-Represents a cyclohexylene group or a single bond. )
【００１０】（２）一般式（１）(2) General formula (1)
【化８】 （ただし（１）式において、Ｒは炭素数１−１６のアル
キル基、アルコキシ基、Ｒ’は炭素数１−１２のアルキ
ル基を示す、環Ａは１，４−フェニレン基または１，４
−シクロヘキシレン基、または単結合を示す。）の化合
物を含有する事を特徴とする液晶組成物。Embedded image (However, in the formula (1), R represents an alkyl group having 1 to 16 carbon atoms, an alkoxy group, R ′ represents an alkyl group having 1 to 12 carbon atoms, and ring A represents 1,4-phenylene group or 1,4
-Represents a cyclohexylene group or a single bond. A liquid crystal composition comprising the compound of the formula (1).
【００１１】（３）一般式（１）(3) General formula (1)
【化９】 （ただし（１）式において、Ｒは炭素数１−１６のアル
キル基、アルコキシ基、Ｒ’は炭素数１−１２のアルキ
ル基を示す、環Ａは１，４−フェニレン基または１，４
−シクロヘキシレン基、または単結合を示す。）の化合
物を含有する液晶組成物を使用してなる液晶素子。Embedded image (However, in the formula (1), R represents an alkyl group having 1 to 16 carbon atoms, an alkoxy group, R ′ represents an alkyl group having 1 to 12 carbon atoms, and ring A represents 1,4-phenylene group or 1,4
-Represents a cyclohexylene group or a single bond. A liquid crystal device using a liquid crystal composition containing the compound of the above).
【００１２】本発明の化合物は環Ａの構造によって以下
の３種類に分けられる。The compounds of the present invention are classified into the following three types according to the structure of ring A.
【００１３】[0013]
【化１０】 Embedded image
【化１１】 Embedded image
【化１２】 Embedded image
【００１４】すなわち、環Ａが１，４−フェニレンの場
合は（１−ａ）、環Ａが１，４−シクロへキシレンのと
きは（１−ｂ）、環Ａが単結合の場合は、（１−ｃ）に
分類できる。Ｒは炭素数１−１６のアルキル基、アルコ
キシ基であるが、炭素数６−１０のアルキル基、アルコ
キシ基が、好ましい。Ｒ’は炭素数１−１２のアルキル
基であるが、炭素数４−８のアルキル基が特に好まし
い。That is, when the ring A is 1,4-phenylene (1-a), when the ring A is 1,4-cyclohexylene (1-b), when the ring A is a single bond, It can be classified into (1-c). R is an alkyl group or an alkoxy group having 1 to 16 carbon atoms, preferably an alkyl group or an alkoxy group having 6 to 10 carbon atoms. R ′ is an alkyl group having 1 to 12 carbon atoms, and an alkyl group having 4 to 8 carbon atoms is particularly preferable.
【００１５】本発明の光学活性化合物と混合して、強誘
電性液晶組成物を構成するのに適している、これまでに
知られた化合物の骨格構造を例示する。The skeleton structure of a compound known so far, which is suitable for forming a ferroelectric liquid crystal composition by mixing with the optically active compound of the present invention, is exemplified.
【００１６】[0016]
【化１３】 Embedded image
【化１４】 Embedded image
【００１７】[0017]
【化１５】 Embedded image
【化１６】 Embedded image
【００１８】化合物の製法 本発明の（１）式の化合物は、以下の経路で好適に製造
できる。Method for Preparing Compound The compound of formula (1) of the present invention can be suitably prepared by the following route.
【００１９】[0019]
【化１７】 Embedded image
【００２０】（式中、Ｒ、Ｒ’環Ａは前述と同様であ
る。）(In the formula, R and R ′ ring A are the same as described above.)
【００２１】すなわち、環Ａに対応した原料（ａ）、環
Ａが１，４−フェニレンの場合は４−置換ビフェニル、
環Ａが１，４−シクロヘキシレンのときは４−置換シク
ロヘキシルベンゼン、環Ａが単結合の場合は、４−置換
ベンゼンをそれぞれ用いて、これに無水塩化アルミニュ
ウムの存在下、無水グルタル酸を作用させ、フリーデル
クラフト反応を行って、３−（４−置換ベンゾイル）ブ
タン酸類（ｂ）を製造できる。この際は、反応溶媒とし
てジクロルメタン、クロロホルム、１，２−ジクロルエ
タンの如きハロゲン化炭化水素、あるいはニトロベンゼ
ン、二硫化炭素等が好適に使用できる。また、この際に
使用できるルイス酸触媒としては、塩化アルミニュウム
の他には塩化鉄等がある。That is, a raw material (a) corresponding to ring A, 4-substituted biphenyl when ring A is 1,4-phenylene,
When ring A is 1,4-cyclohexylene, 4-substituted cyclohexylbenzene is used, and when ring A is a single bond, 4-substituted benzene is used, and glutaric anhydride is acted on in the presence of aluminum chloride anhydrous. Then, a Friedel-Crafts reaction is performed to produce 3- (4-substituted benzoyl) butanoic acids (b). In this case, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, nitrobenzene, carbon disulfide and the like can be suitably used as the reaction solvent. In addition, as the Lewis acid catalyst that can be used at this time, iron chloride and the like are used in addition to aluminum chloride.
【００２２】次に、上述（ｂ）に対して還元剤を用い
て、４−（４−置換フェニル）−ペンタン酸類（ｃ）
が、製造できる。この際の還元剤としては、いわゆるウ
ルフキシュナー還元として知られるＫＯＨ−（ＮＨ2 ）
2 、あるいはヒドロシラン還元剤等が好適に使用でき
る。次に上述（ｃ）に対して、リチウムジイソプロピル
アミド（以下ＬＤＡと略称する）等の塩基によるプロト
ン引き抜きを行い、続いて１，２−エポキシアルカンを
作用させてヒドロキシ酸類（ｄ）が製造できる。通常は
直ちに環化が起こりラクトン類のジアステレオマー混合
物（ｅ）が得られる。該（ｅ）を公知のいづれかの手段
により、ジアステレオマー分離して、表題の化合物
（１）を製造できる。その分離の手段としては、カラム
クロマトクグラフ、高速液体クロマトグラフ等が使用で
きる。Next, 4- (4-substituted phenyl) -pentanoic acids (c) are used for the above (b) by using a reducing agent.
Can be manufactured. As a reducing agent at this time, KOH- (NH 2 ), which is known as so-called Wolf Kishner reduction, is used.
2 or a hydrosilane reducing agent can be suitably used. Next, the above-mentioned (c) is subjected to proton abstraction using a base such as lithium diisopropylamide (hereinafter abbreviated as LDA), and then a 1,2-epoxyalkane is acted thereon to produce hydroxy acids (d). Usually, cyclization occurs immediately to obtain a diastereomer mixture (e) of lactones. The title compound (1) can be produced by diastereomer separation of (e) by any known means. As a means for the separation, a column chromatograph, a high performance liquid chromatograph, or the like can be used.
【００２３】[0023]
【発明の効果】実施例に挙げるように、本発明の化合物
は少量の添加で高速応答の強誘電性液晶組成物を構築で
きた。As described in Examples, the compound of the present invention was able to construct a fast-response ferroelectric liquid crystal composition by adding a small amount thereof.
【００２４】[0024]
実施例１ （２Ｒ、４Ｒ）および（２Ｓ、４Ｒ）−α−３−（４’
−ヘプチルビフェニル−４−イル）プロピル−γ−ブチ
ル−γ−ブチロラクトン 第一段階 ４−（４’−ヘプチルビフェニル−４−イル）−５−オ
キソ−ペンタン酸 アルゴン雰囲気下、無水塩化アルミニュウム（９．０３
ｇ、６７．９ｍｍｏｌ）と無水グルタル酸（２．６１
ｇ、２２．８７ｍｍｏｌ）を加え、アルゴン置換した
後、ＣＨ2 Ｃｌ2 （１５０ｍｌ）を加え０℃に冷却し
た。反応溶液中に、４−ヘプチルビフェニル（４．２６
ｇ、１６．９ｍｍｏｌ）をＣＨ2 Ｃｌ2 （５０ｍｌ）に
溶かした溶液を９０分間で滴下した。同温で３時間攪拌
した後、反応溶液に２％ＨＣｌ（５０ｍｌ）を滴下して
加えた後、ＣＨ2 Ｃｌ2 で抽出し、水及び、飽和食塩水
で洗浄した。無水硫酸マグネシュウムで乾燥し、減圧下
で溶媒を留去して、４−（４’−ヘプチルビフェニル−
４−イル）−５−オキソ−ペンタン酸を得た。 （５．８７ｇ、９５％） 融点 １３２℃ ＴＬＣ Ｒｆ（０．１７） ｓｏｌｖｅｎｔ （ヘキサ
ン：酢酸エチル＝１：１） １Ｈ−ＮＭＲ（４００ＭＨｚ、ＣＤＣｌ３） ８．０２（ｄ，Ｊ＝７．９Ｈｚ，２Ｈ），７．６７
（ｄ，Ｊ＝８．６Ｈｚ，２Ｈ），７．５４（ｄ，Ｊ＝
７．９Ｈｚ，２Ｈ） ７．２７（ｄ，Ｊ＝７．９Ｈｚ，
２Ｈ），３．１０（ｔ，Ｊ＝７．３Ｈｚ，２Ｈ），２．
６５（ｔ，Ｊ＝７・９Ｈｚ，２Ｈ） ２．５２（ｔ，Ｊ
＝７．３Ｈｚ，２Ｈ），２．１１（ｑ，Ｊ＝７．３Ｈ
ｚ，２Ｈ），１．６６−１．２６（１０Ｈ） ０．８８
（ｔ，Ｊ＝７．３Ｈｚ，３Ｈ） １３Ｃ−ＮＭＲ（１００ＭＨｚ，ＣＤＣｌ３） σ １９８．９４，１７８．３９，１４５．８６，１４
３．３６，１３７．１３，１３５．２２，１２９．０
５，１２８．６４，１２７．１２，１２７．０３，３
７．３５，３５．６７，３２．９８，３１．８３，３
１．４５，２９．３２，２９．２０，２２．６８，１
９．１６，１４．１１ ＩＲ（ＣＨＣｌ３） ３６００−２４００（ｗ），３０３０（ｓ），２９４０
（ｍ），２８６０（ｍ），１７１０（ｓ），１６８０
（ｓ），１６０５（ｓ），１４６０（ｍ），１４００
（ｓ），１２９０（ｓ），１２１５（ｓ），１１２０
（ｓ）Example 1 (2R, 4R) and (2S, 4R) -α-3- (4 ′)
-Heptylbiphenyl-4-yl) propyl-γ-butyl-γ-butyrolactone First step 4- (4′-heptylbiphenyl-4-yl) -5-oxo-pentanoic acid Anhydrous aluminum chloride (9. 03
g, 67.9 mmol) and glutaric anhydride (2.61).
g, 22.87 mmol), and after purging with argon, CH 2 Cl 2 (150 ml) was added and the mixture was cooled to 0 ° C. In the reaction solution, 4-heptylbiphenyl (4.26)
g, 16.9 mmol) in CH 2 Cl 2 (50 ml) was added dropwise over 90 minutes. After stirring at the same temperature for 3 hours, 2% HCl (50 ml) was added dropwise to the reaction solution, followed by extraction with CH 2 Cl 2 and washing with water and saturated saline. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 4- (4'-heptylbiphenyl-).
4-yl) -5-oxo-pentanoic acid was obtained. (5.87 g, 95%) Melting point 132 ° C. TLC Rf (0.17) solvent (hexane: ethyl acetate = 1: 1) 1H-NMR (400 MHz, CDCl 3) 8.02 (d, J = 7.9 Hz, 2H) ), 7.67
(D, J = 8.6 Hz, 2H), 7.54 (d, J =
7.9 Hz, 2H) 7.27 (d, J = 7.9 Hz,
2H), 3.10 (t, J = 7.3 Hz, 2H), 2.
65 (t, J = 7.9 Hz, 2H) 2.52 (t, J
= 7.3 Hz, 2H), 2.11 (q, J = 7.3H)
z, 2H), 1.66-1.26 (10H) 0.88
(T, J = 7.3 Hz, 3H) 13 C-NMR (100 MHz, CDCl 3) σ 198.94, 178.39, 145.86, 14
3.36,137.13,135.22,129.0
5,128.64,127.12,127.03,3
7.35, 35.67, 32.98, 31.83, 3
1.45, 29.32, 29.20, 22.68, 1
9.16, 14.11 IR (CHCl3) 3600-2400 (w), 3030 (s), 2940
(M), 2860 (m), 1710 (s), 1680
(S), 1605 (s), 1460 (m), 1400
(S), 1290 (s), 1215 (s), 1120
(S)
【００２５】第二段階 ４−（４’−ヘプチルビフェニル−４−イル）−ペンタ
ン酸 アルゴン雰囲気下、４−（４’−ヘプチルビフェニル−
４−イル）−５−オキソ−ペンタン酸（５．３７ｇ、１
４．７ｍｍｏｌ）をトリフルオロ酢酸（２０ｍｌ）に溶
かし、室温でトリエチルシラン（６．５ｍｌ、４０．７
ｍｍｏｌ）を加え３日間攪拌した。反応溶液に、飽和炭
酸水素ナトリウム水溶液（１００ｍｌ）を加え、ジエチ
ルエーテルで抽出した。有機層を飽和食塩水で洗浄し、
無水硫酸マグネシュウムで乾燥した後、減圧下で溶媒を
留去した。残分をシリカゲルカラムクロマトグラフイー
（ヘキサン：酢酸エチル：ＣＨ2Ｃｌ2 ＝３：１：１）
により分離精製した後ベンゼン及び、ヘキサンで再結晶
し、４−（４’−ヘプチルビフェニル−４−イル）−ペ
ンタン酸（４．２６ｇ、８２％）を得た。 融点 １４３℃ ＴＬＣ Ｒｆ（０．４４） ｓｏｌｖｅｎｔ （ヘキサ
ン：酢酸エチル＝１：１） １Ｈ−ＮＭＲ（４００ＭＨｚ、ＣＤＣｌ３）ｄ σ ７．４９（ｄ，Ｊ＝７．９Ｈｚ，２Ｈ），７．４８
（ｄ，Ｊ＝８．６Ｈｚ，２Ｈ），７．２３（ｄ，Ｊ＝
７．９Ｈｚ，２Ｈ） ７．２２（ｄ，Ｊ＝８．５Ｈｚ，
２Ｈ），２．６６−２．６１（４Ｈ），２．３９（ｔ，
Ｊ＝６．１Ｈｚ，２Ｈ）， １．７３−１．２８（１４
Ｈ），０．８８（ｔ，Ｊ＝６．７Ｈｚ，３Ｈ） １３Ｃ−ＮＭＲ（１００ＭＨｚ，ＣＤＣｌ３） １７９．８１，１４１．８４，１４０．７６，１３８．
８０，１３８．３９，１２８．７６，１２８．７３，１
２６．９２，１２６．８０，３５．６１，３５．１５，
３３．８９，３１．８３，３１．５０，３０．７４，２
９．３５，２９．２１，２４．３２，２２．６８，１
４．１０ ＩＲ（ＣＨＣｌ３） ３６００−２４００（ｗ），２９６０（ｍ），２９３５
（ｓ），２８６０（ｍ），１７１０（ｓ），１４９０
（ｍ），１４６０（ｍ），１２８０（ｍ），１２１０
（ｍ），１１３０（ｍ），１００５（ｍ），８２０
（ｗ）Second step 4- (4'-heptylbiphenyl-4-yl) -pentanoic acid 4- (4'-heptylbiphenyl-pentanoic acid)
4-yl) -5-oxo-pentanoic acid (5.37 g, 1
4.7 mmol) in trifluoroacetic acid (20 ml) and triethylsilane (6.5 ml, 40.7
mmol) and stirred for 3 days. A saturated aqueous solution of sodium hydrogen carbonate (100 ml) was added to the reaction solution, and the mixture was extracted with diethyl ether. Wash the organic layer with saturated saline,
After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue is subjected to silica gel column chromatography (hexane: ethyl acetate: CH 2 Cl 2 = 3: 1: 1)
And recrystallized from benzene and hexane to obtain 4- (4'-heptylbiphenyl-4-yl) -pentanoic acid (4.26 g, 82%). Melting point 143 ° C. TLC Rf (0.44) solvent (hexane: ethyl acetate = 1: 1) 1H-NMR (400 MHz, CDCl 3) d σ 7.49 (d, J = 7.9 Hz, 2H), 7.48
(D, J = 8.6 Hz, 2H), 7.23 (d, J =
7.9 Hz, 2H) 7.22 (d, J = 8.5 Hz,
2H), 2.66-2.61 (4H), 2.39 (t,
J = 6.1 Hz, 2H), 1.73-1.28 (14
H), 0.88 (t, J = 6.7 Hz, 3H) 13C-NMR (100 MHz, CDCl3) 179.81, 141.84, 140.76, 138.
80, 138.39, 128.76, 128.73, 1
26.92, 126.80, 35.61, 35.15,
33.89, 31.83, 31.50, 30.74, 2
9.35, 29.21, 24.32, 22.68, 1
4.10 IR (CHCl3) 3600-2400 (w), 2960 (m), 2935
(S), 2860 (m), 1710 (s), 1490
(M), 1460 (m), 1280 (m), 1210
(M), 1130 (m), 1005 (m), 820
(W)
【００２６】第三段階 （２Ｒ、４Ｒ）および（２Ｓ、４Ｒ）−α−３−（４’
−ヘプチルビフェニル−４−イル）プロピル−γ−ブチ
ル−γ−ブチロラクトン アルゴン雰囲気下、ＴＨＦ（７０ｍｌ）にジイソプロピ
ルアミン（１．３ｍｌ、９．３ｍｍｏｌ）を溶かし、−
７８℃に冷却した後、１．６６Ｎ、ｎ−ブチルリチウム
（５ｍｌ、８．３ｍｍｏｌ）を滴下した。０℃で２０分
間攪拌した後、再び−７８℃に冷却し、反応溶液中に、
４−（４’−ヘプチルビフェニル−４−イル）−ペンタ
ン酸（１．１０ｇ、３．１ｍｍｏｌ）をＴＨＦ（７ｍ
ｌ）に溶かし滴下し、０℃で４０分間攪拌した後、再び
−７８℃に冷却し、（Ｒ）−１，２−エポキシヘプタン
（０．３ｍｌ、２．４９ｍｍｏｌ）をＴＨＦ（２ｍｌ）
に溶かし滴下した。反応溶液を徐々に室温に戻し、飽和
塩化アンモニウムを加え酢酸エチルにて抽出し、有機層
を無水硫酸マグネシウムで乾燥させ、減圧下で溶媒を留
去した。残分をシリカゲルカラムクロマトグラフイー
（ヘキサン：酢酸エチル＝２０：１）により分離し、α
−３−（４’−ヘプチルビフェニル−４−イル）プロピ
ル−γ−ブチル−γ−ブチロラクトン（０．６３ｇ、５
９％）をｔｒａｎｓ体、ｃｉｓ体の混合物として得た。
その後、薄層クロマトグラフイー（ヘキサン：酢酸エチ
ル＝２０：１）によりｔｒａｎｓ（２Ｒ、４Ｒ）、ｃｉ
ｓ（２Ｓ、４Ｒ）体を分離精製した。Third step (2R, 4R) and (2S, 4R) -α-3- (4 ′)
-Heptylbiphenyl-4-yl) propyl-γ-butyl-γ-butyrolactone Under argon atmosphere, diisopropylamine (1.3 ml, 9.3 mmol) was dissolved in THF (70 ml),
After cooling to 78 ° C., 1.66 N, n-butyllithium (5 ml, 8.3 mmol) was added dropwise. After stirring at 0 ° C. for 20 minutes, the mixture was cooled again to −78 ° C.
4- (4'-Heptylbiphenyl-4-yl) -pentanoic acid (1.10 g, 3.1 mmol) was added to THF (7 m
l), the mixture was added dropwise, stirred at 0 ° C for 40 minutes, cooled again to -78 ° C, and (R) -1,2-epoxyheptane (0.3 ml, 2.49 mmol) was added to THF (2 ml).
And added dropwise. The reaction solution was gradually returned to room temperature, saturated ammonium chloride was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was separated by silica gel column chromatography (hexane: ethyl acetate = 20: 1).
-3- (4'-heptylbiphenyl-4-yl) propyl-γ-butyl-γ-butyrolactone (0.63 g, 5
9%) as a mixture of a trans form and a cis form.
Then, trans (2R, 4R), ci by thin layer chromatography (hexane: ethyl acetate = 20: 1).
The s (2S, 4R) form was separated and purified.
【００２７】トランス体（２Ｒ、４Ｒ） 融点 ６２℃ ［α］Ｄ２６ ＋１１．０５°（ｃ＝０．５７，ＣＨＣ
ｌ３） １Ｈ−ＮＭＲ（４００ＭＨｚ、ＣＤＣｌ３） σ ７．５０（ｄ，Ｊ＝７．３Ｈｚ，２Ｈ），７．４８
（ｄ，Ｊ＝７．３Ｈｚ，２Ｈ），７．２３（ｄ，Ｊ＝
７．３Ｈｚ，２Ｈ） ７．２１（ｄ，Ｊ＝７．３Ｈｚ，
２Ｈ），４．４５（ｑ，Ｊ＝６．７Ｈｚ，１Ｈ），２．
６９−２．５７（５Ｈ）， ２．０２（ｄｄ，Ｊ＝６．
７，７．９Ｈｚ，２Ｈ），１．９２−１．８５（ｍ，１
Ｈ），１．７６−１．２９（１９Ｈ），０．９０（ｔ，
Ｊ＝６．７Ｈｚ，３Ｈ），０．８８（ｔ，Ｊ＝６．７Ｈ
ｚ，３Ｈ） １３Ｃ−ＮＭＲ（１００ＭＨｚ，ＣＤＣｌ３） １７９．２０，１４１．８８，１４０．５２，１３８．
８７，１３８．３１，１２８．７７，１２８．７３，１
２６．９３，１２６．７７，７８．７２，３９．２３，
３５．５９，３５．３０，３５．２７，３３．４９，３
１．８１，３１．４９，３０．５４，２９．３３，２
９．１９，２９．１１，２７．４３，２２．６６，２
２．４０，１４．０８，１３．８９ ＩＲ（ＣＨＣｌ３） ３０１０（ｗ），２９３５（ｓ），２８６０（ｓ），１
７６０（ｓ），１５００（ｍ），１４６０（ｍ），１３
８０（ｗ），１３６０（ｍ），１２２０（ｓ），１１８
０（ｍ），１１５０（ｍ），１１２０（ｗ），１００５
（ｍ），９５０（ｗ）Trans form (2R, 4R) Melting point 62 ° C. [α] D26 + 11.05 ° (c = 0.57, CHC
13) 1H-NMR (400 MHz, CDCl3) [sigma] 7.50 (d, J = 7.3 Hz, 2H), 7.48
(D, J = 7.3 Hz, 2H), 7.23 (d, J =
7.3 Hz, 2H) 7.21 (d, J = 7.3 Hz,
2H), 4.45 (q, J = 6.7 Hz, 1H), 2.
69-2.57 (5H), 2.02 (dd, J = 6.
7, 7.9 Hz, 2H), 1.92-1.85 (m, 1
H), 1.76-1.29 (19H), 0.90 (t,
J = 6.7 Hz, 3H), 0.88 (t, J = 6.7H)
z, 3H) 13C-NMR (100 MHz, CDCl3) 179.20, 141.88, 140.52, 138.
87, 138.31, 128.77, 128.73, 1
26.93, 126.77, 78.72, 39.23,
35.59, 35.30, 35.27, 33.49, 3
1.81, 31.49, 30.54, 29.33, 2
9.19, 29.11, 27.43, 22.66, 2
2.40, 14.08, 13.89 IR (CHCl3) 3010 (w), 2935 (s), 2860 (s), 1
760 (s), 1500 (m), 1460 (m), 13
80 (w), 1360 (m), 1220 (s), 118
0 (m), 1150 (m), 1120 (w), 1005
(M), 950 (w)
【００２８】シス体（２Ｓ、４Ｒ） 融点 ９６℃ ［α］Ｄ２６ ＋２６．６７°（ｃ＝０．６３，ＣＨＣ
ｌ３） １Ｈ−ＮＭＲ（４００ＭＨｚ、ＣＤＣｌ３）ｄ σ ７．５０（ｄ，Ｊ＝８．６Ｈｚ，２Ｈ），７．４９
（ｄ，Ｊ＝７．９Ｈｚ，２Ｈ），７．２４（ｄ，Ｊ＝
７．９Ｈｚ，２Ｈ） ７．２２（ｄ，Ｊ＝７．９Ｈｚ，
２Ｈ），４．３１（ｄｄｄｄ，Ｊ＝１１．０，７．３，
５．５，５．５Ｈｚ，１Ｈ）， ２．７０−２．５６
（５Ｈ），２．４２（ｄｄ，Ｊ＝６．７，７．９Ｈｚ，
１Ｈ），２．０４−１．９４（ｍ，１Ｈ），１．７７−
１．２９（２０Ｈ），０．９０（ｔ，Ｊ＝６．７Ｈｚ，
３Ｈ），０．８８（ｔ，Ｊ＝７．３Ｈｚ，３Ｈ） １３Ｃ−ＮＭＲ（１００ＭＨｚ，ＣＤＣｌ３） １７８．７６，１４１．８８，１４０．６２，１３８．
８７，１３８．３４，１２８．７７，１２８．７３，１
２６．９５，１２６．７８，７８．８７，４０．９９，
３５．６１，３５．３６，３５．２４，３１．８３，３
１．４９，３０．０３，２９．３５，２９．２０，２
７．３９，２２．６６，２２．４４，１４．０９，１
３．８９ ＩＲ（ＣＨＣｌ３） ３０１０（ｗ），２９３５（ｓ），２８６０（ｓ），１
７６０（ｓ），１５００（ｍ），１４６０（ｍ），１３
８０（ｗ），１３６０（ｍ），１２２０（ｓ），１１８
０（ｍ），１１５０（ｍ），１１２０（ｗ），１００５
（ｍ），９５０（ｗ）Cis form (2S, 4R) Melting point 96 ° C. [α] D26 + 26.67 ° (c = 0.63, CHC
l3) 1H-NMR (400 MHz, CDCl3) d? 7.50 (d, J = 8.6 Hz, 2H), 7.49
(D, J = 7.9 Hz, 2H), 7.24 (d, J =
7.9 Hz, 2H) 7.22 (d, J = 7.9 Hz,
2H), 4.31 (dddd, J = 11.0, 7.3,
5.5, 5.5 Hz, 1H), 2.70-2.56
(5H), 2.42 (dd, J = 6.7, 7.9 Hz,
1H), 2.04-1.94 (m, 1H), 1.77-
1.29 (20H), 0.90 (t, J = 6.7 Hz,
3H), 0.88 (t, J = 7.3 Hz, 3H) 13C-NMR (100 MHz, CDCl3) 178.76, 141.88, 140.62, 138.
87, 138.34, 128.77, 128.73, 1
26.95, 126.78, 78.87, 40.99,
35.61, 35.36, 35.24, 31.83, 3
1.49, 30.03, 29.35, 29.20, 2
7.39, 22.66, 22.44, 14.09, 1
3.89 IR (CHCl3) 3010 (w), 2935 (s), 2860 (s), 1
760 (s), 1500 (m), 1460 (m), 13
80 (w), 1360 (m), 1220 (s), 118
0 (m), 1150 (m), 1120 (w), 1005
(M), 950 (w)
【００２９】実施例２（組成物例） 以下成分でＳｃ組成物（ｍｉｘｔｕｒｅ Ａ）を調整し
た。その相転移温度は以下のようである。Example 2 (composition example) A Sc composition (mixture A) was prepared with the following components. The phase transition temperature is as follows.
【００３０】[0030]
【化１８】 Embedded image
【００３１】それぞれ濃度は３０、２０、１０、１０、
２０、１０ｗｔ％である。上記組成物９８ｗｔ％および
本発明の実施例１の化合物２ｗｔ％の強誘電性液晶組成
物を調整した。その相転移温度は以下の如くであった。 室温からＳｃ* ６１．１ＳＡ７７．９Ｎ* ８８．２Ｉｓ
ｏ この組成物の２５℃における、自発分極（ｎＣ／ｃｍ
2 ）傾き角（°）および応答時間（μ秒）を測定した。 自発分極（ｎＣ／ｃｍ2 ） ２．１ 傾き角（°） ２１．０ 応答時間（μ秒） １０９．０ このように、本発明の化合物は少量の添加にもかかわら
ず、高速応答の組成物を提供できることが判明した。The concentrations are 30, 20, 10, 10,
20, 10% by weight. A ferroelectric liquid crystal composition of 98 wt% of the above composition and 2 wt% of the compound of Example 1 of the present invention was prepared. The phase transition temperature was as follows. From room temperature to Sc * 61.1SA77.9N * 88.2Is
o Spontaneous polarization of this composition at 25 ° C. (nC / cm
2 ) Tilt angle (°) and response time (μsec) were measured. Spontaneous polarization (nC / cm 2 ) 2.1 Tilt angle (°) 21.0 Response time (μsec) 109.0 Thus, the compound of the present invention has a fast response despite the addition of a small amount. It turned out that it could provide.
【００３２】実施例３（組成物例） メルク社製ネマチック液晶組成物ＺＬＩ−１１３２、１
００重量部に対して本発明の実施例１の化合物を１重量
部添加したカイラルネマッチック液晶組成物を調製し
た。そのカイラルネマチック液晶のピッチ長を各温度で
測定した。Example 3 (Composition example) Nematic liquid crystal composition ZLI-1132, manufactured by Merck & Co., Ltd.
A chiral nematic liquid crystal composition was prepared by adding 1 part by weight of the compound of Example 1 of the present invention to 00 parts by weight. The pitch length of the chiral nematic liquid crystal was measured at each temperature.
【００３３】[0033]
【表１】 [Table 1]
【００３４】以上のように、カイラルピッチ長の温度依
存の少ない液晶組成物が調製できることがわかった。As described above, it was found that a liquid crystal composition having a small temperature dependence of the chiral pitch length could be prepared.
Claims (3)
キル基、アルコキシ基、Ｒ’は炭素数１−１２のアルキ
ル基を示す、環Ａは１，４−フェニレン基または１，４
−シクロヘキシレン基、または単結合を示す。）1. A compound represented by the general formula (1): (However, in the formula (1), R represents an alkyl group having 1 to 16 carbon atoms, an alkoxy group, R ′ represents an alkyl group having 1 to 12 carbon atoms, and ring A represents 1,4-phenylene group or 1,4
-Represents a cyclohexylene group or a single bond. )
キル基、アルコキシ基、Ｒ’は炭素数１−１２のアルキ
ル基を示す、環Ａは１，４−フェニレン基または１，４
−シクロヘキシレン基、または単結合を示す。）の化合
物を含有する事を特徴とする液晶組成物。2. A compound of the general formula (1) (However, in the formula (1), R represents an alkyl group having 1 to 16 carbon atoms, an alkoxy group, R ′ represents an alkyl group having 1 to 12 carbon atoms, and ring A represents 1,4-phenylene group or 1,4
-Represents a cyclohexylene group or a single bond. A liquid crystal composition comprising the compound of the formula (1).
キル基、アルコキシ基、Ｒ’は炭素数１−１２のアルキ
ル基を示す、環Ａは１，４−フェニレン基または１，４
−シクロヘキシレン基、または単結合を示す。）の化合
物を含有する液晶組成物を使用してなる液晶素子。3. General formula (1) (However, in the formula (1), R represents an alkyl group having 1 to 16 carbon atoms, an alkoxy group, R ′ represents an alkyl group having 1 to 12 carbon atoms, and ring A represents 1,4-phenylene group or 1,4
-Represents a cyclohexylene group or a single bond. A liquid crystal device using a liquid crystal composition containing the compound of the above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8311408A JPH10139772A (en) | 1996-11-07 | 1996-11-07 | Optically active lactones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8311408A JPH10139772A (en) | 1996-11-07 | 1996-11-07 | Optically active lactones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH10139772A true JPH10139772A (en) | 1998-05-26 |
Family
ID=18016849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8311408A Pending JPH10139772A (en) | 1996-11-07 | 1996-11-07 | Optically active lactones |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH10139772A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018110406A1 (en) * | 2016-12-12 | 2018-06-21 | Dic株式会社 | Luminescent nanocrystal composite |
-
1996
- 1996-11-07 JP JP8311408A patent/JPH10139772A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018110406A1 (en) * | 2016-12-12 | 2018-06-21 | Dic株式会社 | Luminescent nanocrystal composite |
| JPWO2018110406A1 (en) * | 2016-12-12 | 2019-03-07 | Dic株式会社 | Light emitting nanocrystal complex |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH10147562A (en) | Alkenylazines | |
| US5264150A (en) | Optically active alcohol, process for producing same and liquid crystal compound using same | |
| JPH10139772A (en) | Optically active lactones | |
| US5061398A (en) | Optically active lactone derivative, intermediate therefor, process for producing the intermediate, liquid-crystal composition, and liquid-crystal display device | |
| JP2006063205A (en) | Liquid crystal composition containing trifluoronaphthalene derivative, display element and liquid-crystalline compound, its production method and production intermediate | |
| JP4366737B2 (en) | Fluorine-substituted 4- (3-alkenyl) benzoic acid and its phenyl ester derivative and liquid crystal composition containing the same | |
| US5230830A (en) | Cyanohydrin derivatives and their use in liquid crystal materials and devices | |
| JP3057820B2 (en) | Pyridine derivatives and ferroelectric liquid crystal compositions containing the same | |
| JPH0733353B2 (en) | Halogen-substituted phenylbenzyl ether derivative | |
| JPH11269153A (en) | Optically active diphenylpyrimidine compound | |
| US5171470A (en) | Bifunctional optically active liquid crystal intermediate compound, and process for preparing same | |
| JP3732255B2 (en) | Antiferroelectric liquid crystal compound and antiferroelectric liquid crystal composition containing the compound | |
| JP3101984B2 (en) | Pyrazine derivatives and ferroelectric liquid crystal compositions containing the same | |
| JP3206682B2 (en) | Phenylpyrimidine derivative having optically active cyanocyclopropane ring and liquid crystal composition | |
| US5064564A (en) | Optically active compound, intermediate therefor, process for producing the intermediate, and liquid-crystal composition | |
| JP4193222B2 (en) | Dithiin derivative and liquid crystal composition containing the same | |
| JPH0730051B2 (en) | Liquid crystal compound and liquid crystal composition | |
| JPH02264747A (en) | Carboxylic acid ester compound and liquid crystal compound | |
| JP3194399B2 (en) | Phenylpyrimidine derivative having optically active lactone ring and liquid crystal composition | |
| JPH05271656A (en) | Liquid crystal composition containing phenylpyridine derivative | |
| JPH0759541B2 (en) | Optically active amide compound and smectic liquid crystal composition using the same | |
| JPH08245672A (en) | Liquid crystal mixture, liquid crystal composition containing the same and liquid crystal element | |
| JPH10265442A (en) | Difluorobenzoic acid derivative and liquid crystal composition | |
| JPH07116102B2 (en) | Alkylcyclohexylbiphenyl derivative | |
| JPH05208941A (en) | Nitrogen-containing troponoid liquid crystal |